Mecillinam

Quality 0.50 · 2 views · Updated 2 months ago

Pharmaceutical drug

title: "Mecillinam" type: doc version: 1 created: 2026-02-28 author: "Wikipedia contributors" status: active scope: public tags: ["penicillins", "enantiopure-drugs", "azepanes"] description: "Pharmaceutical drug" topic_path: "general/penicillins" source: "https://en.wikipedia.org/wiki/Mecillinam" license: "CC BY-SA 4.0" wikipedia_page_id: 0 wikipedia_revision_id: 0

::summary Pharmaceutical drug ::

| Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 403346583 | IUPAC_name = (2S,5R,6R)-6-[(E/Z)-(Azepan-1-ylmethylene)amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid | image = Mecillinam skeletal formula.svg | image_class = skin-invert-image | image2 = Mecillinam ball-and-stick model from xtal 1981.png | image_class2 = bg-transparent | drug_name = | tradename = Coactin, Leo, Selexid, Selexidin | Drugs.com = | pregnancy_AU = | pregnancy_US = | pregnancy_category = Appears safe in pregnancy | legal_AU = S4 | legal_CA = | legal_UK = POM | legal_US = | legal_status = Rx-only | routes_of_administration = Intravenous, intramuscular | bioavailability = Negligible | protein_bound = 5 to 10% | metabolism = Some hepatic metabolism | elimination_half-life = 1 to 3 hours | excretion = Renal and biliary, mostly unchanged | CAS_number_Ref = | CAS_number = 32887-01-7 | CAS_supplemental = | ATC_prefix = J01 | ATC_suffix = CA11 | ATC_supplemental = | PubChem = 36273 | DrugBank_Ref = | DrugBank = DB01163 | ChemSpiderID_Ref = | ChemSpiderID = 33357 | UNII_Ref = | UNII = V10579P3QZ | KEGG_Ref = | KEGG = D02888 | ChEMBL_Ref = | ChEMBL = 530 | C=15 | H=23 | N=3 | O=3 | S=1 | smiles = CC1(C@@HC(=O)O)C Mecillinam (INN) or amdinocillin (USAN) is an extended-spectrum penicillin antibiotic of the amidinopenicillin class that binds specifically to penicillin binding protein 2 (PBP2), and is only considered to be active against Gram-negative bacteria. It is used primarily in the treatment of urinary tract infections, and has also been used to treat typhoid and paratyphoid fever. Because mecillinam has very low oral bioavailability, an orally active prodrug was developed: pivmecillinam.

Medical uses

Mecillinam is used in the treatment of infections due to susceptible gram-negative bacteria, especially urinary tract infections which are most commonly caused by Escherichia coli. Mecillinam is active against most pathogenic Gram-negative bacteria, except Pseudomonas aeruginosa and some species of Proteus. Several studies have also found it to be as effective as other antibiotics for treating Staphylococcus saprophyticus infection, though it is Gram-positive, possibly because mecillinam reaches very high concentrations in urine.

Worldwide resistance to mecillinam in bacteria causing urinary tract infection has remained very low since its introduction; a 2003 study conducted in 16 European countries and Canada found resistance to range from 1.2% (Escherichia coli) to 5.2% (Proteus mirabilis). Another large study conducted in Europe and Brazil obtained similar results — 95.9% of E. coli strains, for instance, were sensitive to mecillinam.

Adverse effects

The adverse effect profile of mecillinam is similar to that of other penicillins. Its most common side effects are rash and gastrointestinal upset, including nausea and vomiting.

History

With the codename FL 1060, mecillinam was developed by the Danish pharmaceutical company Leo Pharmaceutical Products (now LEO Pharma). It was first described in the scientific literature in a 1972 paper.

References

References

  1. (August 2000). "Pivmecillinam in the treatment of urinary tract infections". The Journal of Antimicrobial Chemotherapy.
  2. (1985). "Amdinocillin: a novel penicillin. Antibacterial activity, pharmacology and clinical use". Pharmacotherapy.
  3. (July 1976). "Mecillinam: a new antibiotic for enteric fever". British Medical Journal.
  4. (July 1977). "The treatment of enteric fever with mecillinam". The Journal of Antimicrobial Chemotherapy.
  5. (February 2011). "[National S3 guideline on uncomplicated urinary tract infection: recommendations for treatment and management of uncomplicated community-acquired bacterial urinary tract infections in adult patients]". Der Urologe. Ausg. A.
  6. (August 28, 2008). "Amdinocillin (Mecillinam)". [[Johns Hopkins University]].
  7. (January 2003). "An international survey of the antimicrobial susceptibility of pathogens from uncomplicated urinary tract infections: the ECO.SENS Project". The Journal of Antimicrobial Chemotherapy.
  8. (November 2008). "Surveillance study in Europe and Brazil on clinical aspects and Antimicrobial Resistance Epidemiology in Females with Cystitis (ARESC): implications for empiric therapy". European Urology.
  9. (April 1972). "6 -amidinopenicillanic acids--a new group of antibiotics". Nature.
  10. (September 1975). "Mecillinam (FL 1060), a 6beta-amidinopenicillanic acid derivative: bactericidal action and synergy in vitro". Antimicrobial Agents and Chemotherapy.

::callout[type=info title="Wikipedia Source"] This article was imported from Wikipedia and is available under the Creative Commons Attribution-ShareAlike 4.0 License. Content has been adapted to SurfDoc format. Original contributors can be found on the article history page. ::

penicillinsenantiopure-drugsazepanes